7-Deaza-2'-deoxy-7-iodoguanosine
[CAS# 172163-62-1]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Deoxynucleotides and their analogues
• Name: 7-Deaza-2'-deoxy-7-iodoguanosine
• Synonyms: 7-Iodo-7-deaza-2'-deoxyguanosine
• Molecular Formula: C₁₁H₁₃IN₄O₄
• Molecular Weight: 392.15
• CAS Registry Number: 172163-62-1
• EC Number: 899-685-4
• SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C2N=C(NC3=O)N)I)CO)O

Properties

• Solubility: Practically insoluble (0.059 g/L) (25 ºC), Calc.^*
• Density: 2.49±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.919, Calc.^*
• Boiling Point: 679.9±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 365.0±34.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

7-Deaza-2'-deoxy-7-iodoguanosine is a modified purine nucleoside, structurally related to guanosine, which is a naturally occurring nucleoside involved in a wide variety of biological functions such as protein synthesis, energy transfer, and signal transduction. The modification at the 7-position of the purine ring, where a nitrogen atom replaces the conventional carbon atom, enhances the compound's stability and bioactivity. Additionally, the incorporation of a 7-iodo group further impacts the compound's reactivity and makes it a valuable molecule for scientific investigation.

The compound is part of a class of nucleoside analogs, which have been studied for their potential therapeutic applications, particularly in the fields of antiviral and anticancer research. The 2'-deoxy modification ensures that the compound is incorporated into DNA rather than RNA, making it particularly useful in the context of nucleoside analogs designed to interfere with DNA replication.

7-Deaza-2'-deoxy-7-iodoguanosine has been investigated in various studies to explore its effectiveness as a nucleoside analog capable of inhibiting viral replication, particularly for DNA viruses. The compound’s incorporation into viral DNA can potentially lead to chain termination or mutations that disrupt viral replication, making it a promising candidate in antiviral drug discovery.

In addition, as a modified nucleoside, it has been used to investigate the mechanisms of purine metabolism and nucleoside incorporation into nucleic acids. The iodination at the 7-position may also enhance its potential interactions with certain enzymes, including kinases, that are involved in nucleotide metabolism.

The compound has also been studied in the context of cancer therapies. By inhibiting DNA replication and repair, nucleoside analogs like 7-Deaza-2'-deoxy-7-iodoguanosine can exert antitumor effects. These studies have mainly focused on its potential to disrupt cancer cell division by interfering with DNA synthesis, an essential process for cell proliferation.

Despite the chemical's potential, it remains primarily a research compound. Further studies are necessary to fully understand its pharmacokinetic and pharmacodynamic properties, as well as its effectiveness in clinical settings for both antiviral and anticancer treatments.

In conclusion, 7-Deaza-2'-deoxy-7-iodoguanosine is a chemical compound with significant potential in the study of nucleoside analogs, contributing to ongoing research into antiviral and anticancer drugs.